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Florida Keys with Pools(1,765)

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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 4
$1,300 - $1,950
per week

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

Book it Now!
7 night Minimum Stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
  1. Lower Florida Keys >
  2. Key West Condo
#244472
    (61)
    Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 10
    $695 - $855
    per night

    Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10

    Book it Now!
    2 - 4 night Minimum Stay
    • 3 BR,
    • 3 BA,
    • Sleeps 10
    1. Lower Florida Keys >
    2. Key West Condo
    #367100
      (12)
      Charming Condo in Old Town Key West's Truman Annex
        1 Bedrooms,
      • 1 Bathroom
        • , Sleeps 2
      $1,200 - $1,850
      per week

      Charming Condo in Old Town Key West's Truman Annex

      Book it Now!
      7 night Minimum Stay
      • 1 BR,
      • 1 BA,
      • Sleeps 2
      1. Lower Florida Keys >
      2. Key West Condo
      #290407
        (32)
        Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
          2 Bedrooms, Sleeps 4
        $1,300 - $1,950
        per week

        Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!

        Book it Now!
        7 night Minimum Stay
        • 2 BR,
        • Sleeps 4
        1. Lower Florida Keys >
        2. Key West Condo
        #938538
          (18)
          Kawama Yacht Club- Oceanfront Private Beach - Sunsets!
            2 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 8
          $200 - $300
          per night

          Kawama Yacht Club- Oceanfront Private Beach - Sunsets!

          Book it Now!
          3 night Minimum Stay
          • 2 BR,
          • 2 BA,
          • Sleeps 8
          1. Upper Florida Keys >
          2. Key Largo Condo
          #404942vb
            (17)
            Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West
              3 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 10
            $1,800 - $2,900
            per week

            Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West

            7 night Minimum Stay
            • 3 BR,
            • 2 BA,
            • Sleeps 10
            1. Lower Florida Keys >
            2. Key West House
            #317093
              (51)
              Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West
                2 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 6
              $975 - $1,550
              per week

              Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West

              7 night Minimum Stay
              • 2 BR,
              • 2 BA,
              • Sleeps 6
              1. Lower Florida Keys >
              2. Key West House
              #315267
                (45)
                Marathon Luxury Waterfront Pool Home 75' Dock Fully Upgraded
                  2 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 6
                $1,904 - $2,303
                per week

                Marathon Luxury Waterfront Pool Home 75' Dock Fully Upgraded

                Book it Now!
                7 night Minimum Stay
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                1. Central Florida Keys >
                2. Marathon House
                #902566
                  (7)
                  'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..
                    3 Bedrooms,
                  • 2 Bathrooms
                    • , Sleeps 8
                  $400 - $750
                  per night

                  'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..

                  4 night Minimum Stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 8
                  1. Lower Florida Keys >
                  2. Key West Cottage
                  #135603
                    (45)
                    Private Luxury in Prestigious Casa Marina Neighborhood
                      3 Bedrooms,
                    • 3 Bathrooms, 
                    • 1 Half Bath
                      • , Sleeps 7
                    $3,500 - $8,800
                    per month

                    Private Luxury in Prestigious Casa Marina Neighborhood

                    28 night Minimum Stay
                    • 3 BR,
                    • 3 BA,
                    • 1 HF BA,
                    • Sleeps 7
                    1. Lower Florida Keys >
                    2. Key West House
                    #298674
                      (14)
                      Waterfront, Boat Ramp, Pool, Tennis, Golf, Fishing, Diving
                        1 Bedrooms,
                      • 1 Bathroom
                        • , Sleeps 4
                      $125 - $135
                      per night

                      Waterfront, Boat Ramp, Pool, Tennis, Golf, Fishing, Diving

                      Book it Now!
                      3 night Minimum Stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 4
                      1. Central Florida Keys >
                      2. Marathon Condo
                      #910616
                        (5)
                        Full Month Discounts Now Available in Truman Annex, Key West
                          2 Bedrooms,
                        • 2 Bathrooms, 
                        • 1 Half Bath
                          • , Sleeps 5
                        $1,750 - $2,751
                        per week

                        Full Month Discounts Now Available in Truman Annex, Key West

                        7 night Minimum Stay
                        • 2 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 5
                        1. Lower Florida Keys >
                        2. Key West Condo
                        #982960
                          (12)
                          New Home in Gated Community with Oceanview, Pool & Dock! MM21!
                            2 Bedrooms,
                          • 3 Bathrooms
                            • , Sleeps 6

                          New Home in Gated Community with Oceanview, Pool & Dock! MM21!

                          • 2 BR,
                          • 3 BA,
                          • Sleeps 6
                          1. Lower Florida Keys >
                          2. Cudjoe Key House
                          #356519vb
                            (14)
                            Private Yacht 3 blocks from Duval Street & Sloppy Joe's
                              3 Bedrooms, Sleeps 6
                            $575 - $650
                            per night

                            Private Yacht 3 blocks from Duval Street & Sloppy Joe's

                            2 - 5 night Minimum Stay
                            • 3 BR,
                            • Sleeps 6
                            1. Lower Florida Keys >
                            2. Key West Yacht
                            #390580vb
                              (21)
                              Ocean Suite at the Galleon Resort
                                2 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 8
                              $495 - $695
                              per night

                              Ocean Suite at the Galleon Resort

                              Book it Now!
                              2 - 4 night Minimum Stay
                              • 2 BR,
                              • 2 BA,
                              • Sleeps 8
                              1. Lower Florida Keys >
                              2. Key West Condo
                              #929000
                                (4)
                                Oceanfront Condominium - Key West Oceanfront at the Coral Reef
                                  2 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 6
                                $265 - $495
                                per night

                                Oceanfront Condominium - Key West Oceanfront at the Coral Reef

                                4 - 5 night Minimum Stay
                                • 2 BR,
                                • 2 BA,
                                • Sleeps 6
                                1. Lower Florida Keys >
                                2. Key West Condo
                                #154612
                                  (34)
                                  Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon
                                    2 Bedrooms,
                                  • 2 Bathrooms
                                    • , Sleeps 4
                                  $320 - $375
                                  per night

                                  Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon

                                  2 - 3 night Minimum Stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 4
                                  1. Lower Florida Keys >
                                  2. Key West Yacht
                                  #229193
                                    (19)
                                    Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes
                                      1 Bedrooms,
                                    • 1 Bathroom
                                      • , Sleeps 4
                                    $185 - $328
                                    per night

                                    Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes

                                    3 - 5 night Minimum Stay
                                    • 1 BR,
                                    • 1 BA,
                                    • Sleeps 4
                                    1. Lower Florida Keys >
                                    2. Key West Townhome
                                    #3472045
                                      (8)
                                      Beautiful Key Largo Town Home Fully Renovated Top to Bottom
                                        2 Bedrooms,
                                      • 2 Bathrooms
                                        • , Sleeps 6
                                      $180 - $200
                                      per night

                                      Beautiful Key Largo Town Home Fully Renovated Top to Bottom

                                      3 night Minimum Stay
                                      • 2 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                      1. Upper Florida Keys >
                                      2. Key Largo Townhome
                                      #450084vb
                                        (8)
                                        'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..
                                          2 Bedrooms,
                                        • 2 Bathrooms, 
                                        • 1 Half Bath
                                          • , Sleeps 6
                                        $3,300 - $5,500
                                        per week

                                        'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..

                                        7 night Minimum Stay
                                        • 2 BR,
                                        • 2 BA,
                                        • 1 HF BA,
                                        • Sleeps 6
                                        1. Lower Florida Keys >
                                        2. Key West Condo
                                        #390177
                                          (13)
                                          'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...
                                            2 Bedrooms,
                                          • 2 Bathrooms, 
                                          • 1 Half Bath
                                            • , Sleeps 6
                                          $1,950 - $3,500
                                          per week

                                          'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...

                                          7 night Minimum Stay
                                          • 2 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 6
                                          1. Lower Florida Keys >
                                          2. Key West Villa
                                          #390213
                                            (12)
                                            Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower
                                              2 Bedrooms,
                                            • 2 Bathrooms
                                              • , Sleeps 8
                                            $950 - $2,095
                                            per week

                                            Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower

                                            7 night Minimum Stay
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                            1. Upper Florida Keys >
                                            2. Key Largo Condo
                                            #233900
                                              (32)
                                              Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach
                                                2 Bedrooms,
                                              • 2 Bathrooms
                                                • , Sleeps 6
                                              $520 - $525
                                              per night

                                              Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach

                                              Book it Now!
                                              3 night Minimum Stay
                                              • 2 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                              1. Lower Florida Keys >
                                              2. Key West House
                                              #3498085
                                                (3)
                                                'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...
                                                  2 Bedrooms,
                                                • 2 Bathrooms
                                                  • , Sleeps 6
                                                $2,100 - $3,800
                                                per week

                                                'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...

                                                7 night Minimum Stay
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 6
                                                1. Lower Florida Keys >
                                                2. Key West Condo
                                                #390175
                                                  (23)
                                                  *$1350 wk 3/2.5 Lg Gulfside House with Dock & Cabana Club
                                                    3 Bedrooms,
                                                  • 2 Bathrooms, 
                                                  • 1 Half Bath
                                                    • , Sleeps 8
                                                  $1,350 - $2,095
                                                  per week

                                                  *$1350 wk 3/2.5 Lg Gulfside House with Dock & Cabana Club

                                                  7 night Minimum Stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 8
                                                  1. Central Florida Keys >
                                                  2. Marathon House
                                                  #186293
                                                    (48)
                                                    'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...
                                                      2 Bedrooms,
                                                    • 2 Bathrooms, 
                                                    • 1 Half Bath
                                                      • , Sleeps 5
                                                    $2,950 - $5,000
                                                    per week

                                                    'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...

                                                    7 night Minimum Stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 5
                                                    1. Lower Florida Keys >
                                                    2. Key West Condo
                                                    #904145
                                                      (19)
                                                      Oceanfront resort condo beautifully renovated. Ocean & Marina views Free WI-FI
                                                        2 Bedrooms,
                                                      • 2 Bathrooms
                                                        • , Sleeps 6
                                                      $1,080 - $1,380
                                                      per week

                                                      Oceanfront resort condo beautifully renovated. Ocean & Marina views Free WI-FI

                                                      7 night Minimum Stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 6
                                                      1. Upper Florida Keys >
                                                      2. Key Largo Condo
                                                      #172415
                                                        (25)
                                                        'PARADISE @ GARRISON BIGHT': Large 5BR/4BA Waterfront Home + Private Dock...
                                                          5 Bedrooms,
                                                        • 4 Bathrooms
                                                          • , Sleeps 14
                                                        $1,200 - $1,800
                                                        per night

                                                        'PARADISE @ GARRISON BIGHT': Large 5BR/4BA Waterfront Home + Private Dock...

                                                        4 night Minimum Stay
                                                        • 5 BR,
                                                        • 4 BA,
                                                        • Sleeps 14
                                                        1. Lower Florida Keys >
                                                        2. Key West Townhome
                                                        #390212
                                                          (25)
                                                          Luxury Home with Pool, Hot Tub & 50' Dock. Spectacular Gulf View.
                                                            3 Bedrooms,
                                                          • 3 Bathrooms
                                                            • , Sleeps 8
                                                          $2,300 - $3,500
                                                          per week

                                                          Luxury Home with Pool, Hot Tub & 50' Dock. Spectacular Gulf View.

                                                          7 night Minimum Stay
                                                          • 3 BR,
                                                          • 3 BA,
                                                          • Sleeps 8
                                                          1. Central Florida Keys >
                                                          2. Marathon House
                                                          #900688
                                                            (18)
                                                            World-Class Private Retreat Compound - Over 300' Waterfront- 152' Dock
                                                              7 Bedrooms,
                                                            • 6 Bathrooms
                                                              • , Sleeps 14
                                                            $7,000
                                                            per week

                                                            World-Class Private Retreat Compound - Over 300' Waterfront- 152' Dock

                                                            Book it Now!
                                                            7 night Minimum Stay
                                                            • 7 BR,
                                                            • 6 BA,
                                                            • Sleeps 14
                                                            1. Upper Florida Keys >
                                                            2. Key Largo Estate
                                                            #3482337
                                                              • 1 - 30 of 1,765
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